WO1999005122A1 - Derives d'acide pyrimidyloxyphenylacetique - Google Patents

Derives d'acide pyrimidyloxyphenylacetique Download PDF

Info

Publication number
WO1999005122A1
WO1999005122A1 PCT/EP1998/004258 EP9804258W WO9905122A1 WO 1999005122 A1 WO1999005122 A1 WO 1999005122A1 EP 9804258 W EP9804258 W EP 9804258W WO 9905122 A1 WO9905122 A1 WO 9905122A1
Authority
WO
WIPO (PCT)
Prior art keywords
cyclohexylmethyl
hydrogen
methyl
carbon atoms
halogen
Prior art date
Application number
PCT/EP1998/004258
Other languages
German (de)
English (en)
Inventor
Ulrich Heinemann
Herbert Gayer
Peter Gerdes
Ralf Tiemann
Astrid Mauler-Machnik
Stefan Dutzmann
Klaus Stenzel
Original Assignee
Bayer Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU88069/98A priority Critical patent/AU8806998A/en
Priority to EP98939627A priority patent/EP1000037A1/fr
Priority to JP2000504121A priority patent/JP2001510832A/ja
Priority to US09/462,797 priority patent/US6348471B1/en
Publication of WO1999005122A1 publication Critical patent/WO1999005122A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • the invention relates to new pyrimidyloxyphenylacetic acid derivatives, several processes for their preparation and their use as fungicides, as well as new intermediates and a process for their production.
  • R stands for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, with the exception of 2,2,2-trifluoroethyl and l-methyl-2,2,2-trifluoroethyl, Q represents oxygen or -NH-, and
  • I_ 1, Lp-, iß and IJ * are the same or different and are each independently hydrogen, halogen, cyano, nitro, each optionally substituted by halogen-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl
  • saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkynyl
  • the saturated or unsaturated hydrocarbon chains are in each case straight-chain or branched, also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine
  • Cycloalkyl stands for saturated, carbocyclic, ring-shaped compounds which optionally form a polycyclic ring system with further carbocyclic, fused or bridged rings
  • Cycloalkenyl stands for carbocyclic, ring-shaped compounds which contain at least one double bond and optionally form a polycyclic ring system with further carbocyclic, fused or bridged rings
  • R 1 represents alkyl or arylalkyl
  • the substances according to the invention show a better fungicidal activity than 2- (methoxyimino) -2 - [[4- (2,2,2-trifluoroethoxy) -2-pyrimidinyl] oxy] -phenylacetic acid methyl ester, 2- (methoxyimino) -N -methyl-2 - [[4- (2,2,2-trifluoroethoxy) -2-pyrimidinyl] oxy] phenylacetamide, 2- (methoxyimino) -2 - [[4- (2,2,2-trifluoro-1 -methyl-ethoxy) -2-pyrimidinyl] oxy] -phenylacetic acid methyl ester and 2- (methoxyimino) -N-methyl-2 - [[4- (2,2,2-trifluoro-l-methylethoxy) -2-pyrimidinyl] oxy ] -phenylacetamide, which are constitutionally similar, previously known active ingredients
  • the compounds of the invention can optionally be used as mixtures of various possible isomeric forms, in particular stereoisomers, such as. B. E and Z, or optical isomers are present. Both the E and the Z isomers, the individual enantiomers, the racemates and any mixtures of these isomers are claimed.
  • Ll, iß, iß and L 4 are the same or different and are each independently hydrogen, halogen, cyano, nitro, each optionally substituted by 1 to 5 halogen atoms alkyl, alkoxy, alkylthio, alkylsulfinyl or
  • Alkylsulfonyl each having 1 to 6 carbon atoms, preferably for
  • R for methyl which is optionally mono-, disubstituted or trisubstituted by halogen or optionally mono-, disubstituted, disubstituted, quadruplicate or pentavalent by halogen and / or 1 to 2 alkoxy groups having 1 to 8 carbon atoms, or optionally disubstituted by one, two, three or four times , fivefold, sixfold or sevenfold n-propyl substituted by halogen and / or 1 to 2 alkoxy groups with 1 to 8 carbon atoms or for optionally single, twofold, fourfold, fivefold, sixfold or sevenfold by halogen and / or 1 or 2 alkoxy groups with 1 to 8 carbon atoms substituted i-propyl,
  • ß, ß, ß and ß are the same or different and are independently hydrogen, halogen, cyano, nitro, each optionally substituted by 1 to 5 halogen atoms alkyl, alkoxy, alkylthio, alkylsulfinyl or Alkylsulfonyl each having 1 to 6 carbon atoms, preferably hydrogen or methyl and in particular hydrogen.
  • R for optionally single to n-fold (where n stands for the number of hydrogen atoms of the respective unsubstituted hydrocarbon radical) by halogen and / or 1 to 2 alkoxy groups with 1 to 8 carbon atoms and / or 1 to 2 cycloalkyl groups with 3 to 6 carbon atoms (the in turn in turn optionally substituted by halogen, alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 halogen atoms or haloalkenyl with 2 to 4 carbon atoms and 1 to 3 halogen atoms) or substituted alkenyl) Alkynyl having 2 to 12 carbon atoms,
  • iß, ß, iß and iß are the same or different and are each independently hydrogen, halogen, cyano, nitro, each optionally substituted by 1 to 5 halogen atoms alkyl, alkoxy, alkylthio, alkylsulfinyl or
  • Alkylsulfonyl each having 1 to 6 carbon atoms, preferably for
  • R represents cycloalkyl, cycloalkenyl which is optionally mono- to pentasubstituted by halogen, alkyl having 1 to 4 carbon atoms, alkenyl having 2 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms or haloalkenyl having 2 to 4 carbon atoms and 1 to 3 halogen atoms , Cycloalkylalkyl or cycloalkenylalkyl with 3 to 8 carbon atoms in the cycloalkyl or cycloalkenyl part and 1 to 4 carbon atoms in the alkyl part,
  • iß, ß xm ⁇ lß are the same or different and are independently hydrogen, halogen, cyano, nitro, each optionally substituted by 1 to 5 halogen atoms alkyl, alkoxy, alkylthio, alkylsulfinyl or
  • Alkylsulfonyl each having 1 to 6 carbon atoms, preferably hydrogen or methyl and in particular hydrogen.
  • R for optionally single to n-fold (where n stands for the number of hydrogen atoms of the respective unsubstituted hydrocarbon radical) by fluorine, chlorine or bromine and / or n-, i-, s- or t- substituted once to twice by methoxy or ethoxy Butyl, 1-, 2-, 3-, neo-pentyl, 1-, 2-, 3-, 4- (2-methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3- , 4-, 5- (2-methylpentyl), 1-, 2-, 3- (3-methylpentyl), 2-ethylbutyl, 1-, 3-, 4- (2,2-dimethylbutyl), 1-, 2nd - (2,3-dimethylbutyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl,
  • iß, iß, iß and iß are the same or different and are each independently hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoromethyl, difluorifluoromethyl, difluorifluoromethyl, difluorifluoromethyl, difluoromethyl, difluorifluoromethyl, difluoromethyl, difluoromethyl, difluoromethyl sulf
  • R for methyl which is optionally mono-, disubstituted or trisubstituted by fluorine, chlorine or bromine or optionally mono-, disubstituted, in four, or five times by fluorine, chlorine, bromine and / or ethyl which is monosubstituted or disubstituted by methoxy or ethoxy, or optionally, monosubstituted or double , triple, quadruple, fivefold, sixfold or sevenfold by fluorine, chlorine, bromine and / or n-propyl substituted once or twice by methoxy or ethoxy or for optionally single, double, fourfold, fivefold, sixfold or sevenfold by fluorine, chlorine, bromine and / or i-propyl which is mono- to disubstituted by methoxy or ethoxy,
  • L *, L.2, L- and L 4 are identical or different and are each independently of one another hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoromethio, trifluoromifluoromethyl, trifluoromifluoromethyl, Trifluoromethylsulfinyl or trifluoromethylsulfonyl, preferably hydrogen or methyl and in particular hydrogen.
  • I_ I, ß, ß and L 4 are the same or different and are each independently hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,
  • I_l, iß, iß and L 4 are the same or different and are each independently hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy,
  • radical definitions specified for these radicals in the respective combinations or preferred combinations of radicals are independently replaced by radical definitions of other preferred ranges, regardless of the combination specified in each case.
  • Formula (II) provides a general definition of the 4-halo-2-phenoxypyrimidines required as starting materials for carrying out process a) according to the invention.
  • Q, ⁇ , ß, ß and ß preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for Q, ß, ß, ß and ß were specified.
  • X represents halogen, preferably chlorine.
  • the 4-halo-2-phenoxypyrimidines of the formula (II) are not yet known; they are also the subject of the present application as new substances.
  • R 2 represents alkyl or arylalkyl
  • Formula (V) optionally in the presence of a diluent and optionally in the presence of an acid acceptor.
  • Formula (VI) provides a general definition of the 4-halo-2-alkylsulfonylpyrimidines required as starting materials for carrying out process c) according to the invention.
  • X preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for X in connection with the description of the intermediates of the formula (II) according to the invention.
  • R 2 represents alkyl or arylalkyl, preferably methyl or benzyl.
  • the 4-halo-2-alkylsulfonylpyrimidines of the formula (VI) are known and can be prepared by known processes (see, for example, Heterocycles (1985), 23 (3), 611-16).
  • Formula (V) provides a general definition of the 2- (l-hydroxyphenyl-l-methoximino) acetic acid derivatives which are further required as starting materials for carrying out process c) according to the invention.
  • Q, iß, L 2 , iß and iß preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for Q.
  • I_l, L 2 , iß and iß were specified.
  • the 2- (l-hydroxyphenyl-l-methoximino) acetic acid derivatives of the formula (V) are known and can be prepared by known processes (see, for example,
  • Formula (III) provides a general definition of the alcohols required as starting materials for carrying out process a) according to the invention.
  • R preferably or in particular has those meanings which have already been stated as preferred or as particularly preferred for R in connection with the description of the compounds of the formula (I) according to the invention.
  • the alcohols of the formula (III) are known synthetic chemicals.
  • Formula (IV) provides a general definition of the alkylsulfonylpyrimidines required as starting materials for carrying out process b) according to the invention.
  • R preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for R in connection with the description of the compounds of the formula (I) according to the invention.
  • R ⁇ represents alkyl or arylalkyl, preferably methyl or benzyl.
  • alkylsulfonylpyrimidines of the formula (IV) are known and can be prepared by known processes (compare, for example, WO 95-24396 or Chem. Ber., 101,
  • Suitable diluents for carrying out processes a), b) and c) are all inert organic solvents. These preferably include ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile;
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Sulfoxides, such as dimethyl sulfoxide; or sulfones, such as sulfolane.
  • Processes a), b) and c) according to the invention are optionally carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor All conventional inorganic or organic bases are suitable as such. These preferably include alkaline earth metal or alkali metal hydrides, amides, hydroxides, alcoholates, carbonates, hydrogen carbonates, and alkaline earth metal or alkali metal alkyl compounds, such as sodium hydride, sodium amide, potassium tert-butoxide, sodium hydroxide,
  • Potassium hydroxide sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or butyllitium.
  • reaction temperatures can be varied within a substantial range when carrying out processes a), b) and c). In general, temperatures from -20 ° C to 130 ° C, preferably at temperatures from -10 ° C to 80 ° C.
  • the processes according to the invention are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar
  • reaction is carried out, worked up and isolated by the generally customary processes (see also the preparation examples).
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria
  • Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacte ⁇ aceae, Corynebacte ⁇ aceae and Streptomycetaceae
  • pathogens of fungal and bacterial are exemplary but not limiting
  • Xanthomonas species such as, for example, Xanthomonas campest ⁇ s pv oryzae
  • Pseudomonas species such as, for example, Pseudomonas sy ⁇ ngae pv lachrymans,
  • Erwinia species such as, for example, Erwinia amylovora,
  • Pythium species such as Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae,
  • Peronospora species such as, for example, Peronospora pisi or P brassicae,
  • Erysiphe species such as, for example, Erysiphe gramrnis,
  • Sphaerotheca species such as, for example, Sphaerotheca bowinea
  • Podosphaera species such as, for example, Podosphaera leucot ⁇ cha,
  • Ventu ⁇ a species such as, for example, Ventu ⁇ a inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P graminea
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea
  • Septoria species such as, for example, Septoria nodorum
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens
  • Alternaria species such as, for example, Alternaria brassicae;
  • Pseudocercosporella species such as, for example, Pseudocercosporella herpotrichoides.
  • the fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
  • the active compounds according to the invention can be particularly successful
  • the active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV - Cold and warm fog formulations.
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions
  • alcohols such as butanol or glycol, and the like their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfone oxide, as well as water.
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • Possible solid carriers are: for example, natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates.
  • Solid carrier materials for granules come into question: e.g.
  • broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and
  • emulsifiers and / or foaming agents are: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are: e.g. Lignin liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum mariabicum, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and
  • Zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds can be converted into the customary formulations, such as Solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine capsules in polymeric substances and in coating compositions for seeds, as well as ULV cold and warm mist formulations.
  • customary formulations such as Solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine capsules in polymeric substances and in coating compositions for seeds, as well as ULV cold and warm mist formulations.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Debacarb dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomo h, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxinodonine, dithorphononodine
  • Ediphenphos Epoxiconazole, Etaconazole, Ethirimol, Etridiazole, Famoxadone, Fenapanil, Fenarimol, FenbuconazoL, Fen Nameam, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flurprimol, Flusilazidol, Flusilazidol, Flusilazidol, Flusilazidol, Flusilazid, Flusilazid, Flusilazid, Flusilazid, Flusilazid Fosetyl sodium, fthalide, fuberidazole,
  • Imazalil Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl,
  • Metconazole methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,
  • Paclobutrazole Pe.azoat, Penconazol, Pencycuron, Phosdiphen, Pimaricin, Piperalin, Polyoxin, Polyoxorim, probenazole, Prochloraz, Procymidon, Propamocarb, Propanosine-Sodium, Propiconazole, Propineb, Pyrazophos, Pyrifen, Pyifen, Pyroquilanil
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole, thicyofen,
  • Thifluzamide Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazbutil, Triazoxid, Trichlamid, Tricyclazol, Tridemo ⁇ h, Triflumizol, Triforin, Triticonazole,
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil,
  • Fluazinam Fluazuron, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,
  • Parathion A Parathion M, Peimethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenophos, Promecarb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymethosphos, Pyridlhrin, Pyridlhrin, Pyridlhrin, Pyridlhrin, Pyridlhrin, Pyridlhrin, Pyridlhrin, Pyridlpyrrethrum, Pyridaben, Pyrirnidifen, Pyriproxifen,
  • Tebufenozide Tebufenpyrad
  • Tebupirimiphos Teflubenzuron
  • Tefluthrin Temephos
  • Terbam Terbufos
  • Tetrachlorvinphos Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuringiensin, Tralomenhriazon, Tralomenhriazon, Tronomenhrononium,
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to prepare the active ingredient or the
  • the application rates can be varied within a relatively wide range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0, 1% aqueous phosphoric acid)
  • Solvent 25 parts by weight of N, N-dimethylacetamide emulsifier: 0.6 part by weight of alkylaryl polyglycol ether
  • Active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • the compounds of preparation examples (3) and (129) show an efficiency of 100% compared to the untreated control at an exemplary application rate of active ingredient of 125 g / ha.
  • Example B
  • Emulsifier 0.6 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • the compounds of preparation examples (3) and (129) show an efficiency of 100% compared to the untreated control at an exemplary application rate of active ingredient of 125 g / ha.
  • Example C
  • Emulsifier 0.6 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are placed in a greenhouse at a temperature of approx. 15 ° C and a relative humidity of approx. 80%.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • the compound of preparation example (1) at an exemplary application rate of active ingredient of 125 g / ha has an efficiency of more than 60% compared to the untreated control.
  • the known compounds achieve 2- (methoxyimino) -2 - [[4- (2,2,2-trifluoroethoxy) -2-pyrimidinyl] oxy] phenylacetic acid methyl ester, 2- (methoxyimino) -N-methyl-2- [[4- (2,2,2-tri-fluoroethoxy) -2-pyrimidinyl] oxy] phenylacetamide, 2- (methoxyimino) -N-methyl-2 - [[4- (2,2,2-trifluoro- l-methylethoxy) -2-pyrimidinyl] oxy] phenylacetamide under the same
  • Emulsifier 0.6 part by weight of alkylaryl polyglycol ether
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80%
  • the compound of preparation example (1) shows an efficiency of 70% compared to the untreated control at an exemplary application rate of active ingredient of 250 g / ha.
  • the known compounds achieve 2- (methoxyimino) -2 - [[ 4- (2,2,2-trifluoroethoxy) -2-pyrimidinyl] oxy] - phenylacetic acid, methyl ester, 2- (methoxyimino) -N-methyl-2 - [[4- (2,2,2-trifluoroethoxy) -2 -pyrimidinyl] oxy] -phenylacetamide, 2- (methoxyimino) -2 - [[4- (2,2,2-trifluoro-1-methylethoxy) -2-pyrimidinyl] oxy] -phenylacetic acid methyl ester and 2- (methoxy-imino) -N-methyl-2 - [[4- (2,2,2-trifluoro-l-methylethoxy) -2-pyrpyrimidinyl]
  • Emulsifier 3 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 3 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • the compounds of preparation examples (3) and (129) show an efficiency of at least 75% compared to the untreated control at an exemplary application rate of active ingredient of 100 g / ha.
  • the known compounds achieve 2- (methoxyimino) -2 - [[4- (2,2,2-trifluoroethoxy) -2-pyrimidinyl] oxy] phenylacetic acid methyl ester and 2- (methoxyimino) -N-methyl-2- [[4- (2,2,2-trifluoro-1-methylethoxy) -2-pyrimidinyl] oxy] phenylacetamide under the same conditions only efficiencies below 70%.
  • Example F Example F
  • Emulsifier 3 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • the compound of preparation example (3) shows an efficiency of at least 80% at an exemplary application rate of active ingredient of 10 g / ha compared to the untreated control.
  • the known compounds achieve 2- (methoxyimino) -2 - [[4- (2,2,2-trifluoroethoxy) -2-pyrimidinyl] oxy] phenylacetic acid methyl ester, 2- (methoxyimino) -N-methyl-2- [[4- (2,2,2-tri-fluoroethoxy) -2-pyrimidinyl] oxy] phenylacetamide, 2- (methoxyimino) -2 - [[4- (2,2,2-tri-fluoro-l- methylethoxy) -2-pyrimidinyl] oxy] phenylacetic acid and 2- (methoxyimino) -N-methyl-2 - [[4- (2,2,2-trifluoro-l-methylethoxy) -2-pyrimidinyl] oxy] pheny
  • Emulsifier 3 parts by weight of alkylaryl polyglycol ether
  • the plants are then placed in the greenhouse at approx. 21 ° C. and a relative humidity of approx. 90%.
  • Evaluation is carried out 12 days after the inoculation. 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne de nouveaux dérivés d'acide pyrimidyloxyphénylacétique, plusieurs procédés permettant de produire ces derivés et l'utilisation de ceux-ci comme fongicides, ainsi que de nouveaux produits intermédiaires et un procédé permettant leur production.
PCT/EP1998/004258 1997-07-22 1998-07-09 Derives d'acide pyrimidyloxyphenylacetique WO1999005122A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU88069/98A AU8806998A (en) 1997-07-22 1998-07-09 Pyrimidyl oxyphenylacetic acid derivatives
EP98939627A EP1000037A1 (fr) 1997-07-22 1998-07-09 Derives d'acide pyrimidyloxyphenylacetique
JP2000504121A JP2001510832A (ja) 1997-07-22 1998-07-09 ピリミジルオキシフェニル酢酸誘導体
US09/462,797 US6348471B1 (en) 1997-07-22 1998-07-09 Pyrimidyl oxyphenylacetic acid derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19731322.1 1997-07-22
DE19731322A DE19731322A1 (de) 1997-07-22 1997-07-22 Pyrimidyloxyphenylessigsäurederivate

Publications (1)

Publication Number Publication Date
WO1999005122A1 true WO1999005122A1 (fr) 1999-02-04

Family

ID=7836435

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/004258 WO1999005122A1 (fr) 1997-07-22 1998-07-09 Derives d'acide pyrimidyloxyphenylacetique

Country Status (6)

Country Link
US (1) US6348471B1 (fr)
EP (1) EP1000037A1 (fr)
JP (1) JP2001510832A (fr)
AU (1) AU8806998A (fr)
DE (1) DE19731322A1 (fr)
WO (1) WO1999005122A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995024396A1 (fr) * 1994-03-07 1995-09-14 Zeneca Limited Fongicides a base de pyrimidine

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2097583T3 (es) 1989-05-17 1997-04-01 Shionogi & Co Procedimiento de preparacion de derivados de alcoxiiminoacetamida y un intermediario de este procedimiento.
GB9016584D0 (en) * 1990-07-27 1990-09-12 Ici Plc Fungicides
GB9023292D0 (en) 1990-10-25 1990-12-05 Ici Plc Fungicides

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995024396A1 (fr) * 1994-03-07 1995-09-14 Zeneca Limited Fongicides a base de pyrimidine

Also Published As

Publication number Publication date
DE19731322A1 (de) 1999-01-28
AU8806998A (en) 1999-02-16
US6348471B1 (en) 2002-02-19
EP1000037A1 (fr) 2000-05-17
JP2001510832A (ja) 2001-08-07

Similar Documents

Publication Publication Date Title
EP0937050A1 (fr) Halogenopyrimidinylaryl(thio)ethers utilises comme pesticides
EP0915863B1 (fr) Carboxamides de dihydrofurane
EP0915852A1 (fr) Derives de 1,3-dimethyle-5-fluor-pyrazol-4-carboxamide, leur preparation et leur utilisation comme microbicides
EP1003742A1 (fr) Methoximinomethyloxadiazines utilisees comme pesticides
WO1998055461A1 (fr) Composes du type fluoromethoximino
EP1107956A2 (fr) Utilisation de derives de 5-amino-pyrazol pour lutter contre des micro-oranismes
DE19818313A1 (de) Azine
EP0984948A1 (fr) Sulfonyloxadiazolones
EP1095014B1 (fr) Derives de methoxy-imino-phenylacetamide et leur utilisation comme pesticides
WO1999046263A2 (fr) Benzoheterocyclyloximes fongicides
EP1115723A2 (fr) Methoximinomethyloxathiazines
EP0973770A1 (fr) Methoximinomethyldioxazine fungicides
EP0970061A1 (fr) Derives de dioxazine d'alcoximinomethyle a action fungicide
WO1999019311A1 (fr) Azines contenant le groupe 5,6-dihydro-(1,4,2)dioxazine-3-yle et leur utilisation comme fongicides
WO1999005122A1 (fr) Derives d'acide pyrimidyloxyphenylacetique
WO1999019312A1 (fr) Derives de 1,4,2-dioxazine microbicides
WO1998040351A1 (fr) Derives d'esters de phenyle d'acide acrylique
WO1999007686A1 (fr) Derive de triazoline-thione et son utilisation comme microbicide
DE19917784A1 (de) Verwendung von 2,4-Diamino-pyrimidin-Derivaten zur Bekämpfung von Mikroorganismen
DE19805611A1 (de) Azine

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE GH GM HR HU ID IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW SD SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 1998939627

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 09462797

Country of ref document: US

NENP Non-entry into the national phase

Ref country code: KR

WWP Wipo information: published in national office

Ref document number: 1998939627

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

NENP Non-entry into the national phase

Ref country code: CA

WWW Wipo information: withdrawn in national office

Ref document number: 1998939627

Country of ref document: EP